One example of the kind of behavior that hurt Mr. Sinofsky’s standing at the company occurred this year at a two-day retreat for Microsoft’s senior executives at the Semiahmoo resort on the coast just below the Canadian border in Washington State. At the meeting, Microsoft’s various division heads were expected to make presentations on their businesses, answer questions and remain to hear their peers repeat the exercise.

When Mr. Sinofsky stood on the first day to speak about the Windows division, he told the group he had not prepared a presentation, and if they wanted to catch up on the progress of Windows 8, they could read his company blog, where he publicly chronicled the software’s development. He answered questions from the audience and then left the resort, while his colleagues remained until the next day, according to multiple people who were present.